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Thoreau's in Wequassett Inn Resort and Golf Club , and right next door to Twenty Eight Atlantic, is a club like atmosphere in a serene resort setting. It is furnished with leather chairs and a stone granite fireplace, that lends it a look right out of a detective movie. This place fits into Pleasant Bay with its decor and a menu all its own and a long list of wines and cocktails.

Hog Island Beer Co. is a beautiful beer garden near the shores at Orleans. The pub offers its finest and freshly brewed beer made in their own brewery. They have some signature beers that go down well with some comfort foodlike clam chowder and pretzels. Visit this picturesque place and enjoy your time relaxing while you sip on some fine bubbling beer.

Set at the heart of Orleans, Mahoney's Atlantic is one of the best drinking and dining spots around town. Peppered with chic wooden tones, a high arched roof and cozy cubicles, this is an ideal place for a causal yet intimate meal and a round of drinks. Its menu is dominated by local-inspired dishes, with a selection of seafood and contemporary favorites. The popular Roasted Chicken, Blackened Salmon and Atlantic Steaming Bowl are not-to-be-missed, while the Sirloin Steak and Barbecued Ribs are also well-worth a shot. In addition, this place is also known for its signature cocktails, of which the Blue Lemon Drop, Pineapple Train Wreck and Goosed Ginger top the popularity list.

The iconic red house on Main Street is home to Red Nun Bar & Grill which has been a favorite hangout for locals. The wooden interiors and a bar TV create a casual and relaxing ambiance perfect for unwinding after work. The American fare served here are quite delicious and filling. Red Nun's fish and chips are said to be amongst the best in town and hence a must try for all. The bar offers a variety of beers on tap as well as other spirits. The bar hosts karaoke events during weekends which fun and great for socializing with the locals. The fun-filled ambiance and spacious outdoor seating make the Red Nun Bar & Grill ideal for casual drinks on a lazy afternoon.

Una parte di questo rinomato posto è un ristorante in vecchio stile con moquette rossa e separè, l'altra è un enorme bar e sala dove mischiarsi alla folla. Il cibo è buono in entrambi: nella sala da pranzo bistecche, pesce e chowder (zuppe locali), mentre nel bar le proposte sono più leggere dato che l'attenzione è più sui drinks. I ristoranti a Cape Cod aprono e chiudono, ma il Chatham Squire rimane il posto dove mangiare un boccone e bersi qualcosa con gli amici.

As the name suggests, Local Break offers a refreshing break to those looking for local draft beers and some wholesome food. The creative cocktails and delicious home-made sangria served here are exceptional. The food menu features a contemporary twist on traditional American classics made with fresh and local ingredients. The restaurant also has a daily specials menu for those looking for something different. A spacious bar with tall chairs make the Local Break perfect for mingling with the locals and making new friends. The casual and inviting atmosphere of the bar along with friendly bartenders, are sure to make you stay for one more drink.